Wilmington Antique & Flea Market stands as southern Vermont's largest weekend flea market, operating continuously since 1983 with over 42 years of family-owned tradition along scenic Route 9 between Brattleboro and Bennington. This sprawling 10-acre outdoor antique market welcomes visitors every Saturday and Sunday from 8:00 AM to 3:00 PM, mid-May through mid-October, with extended Monday hours during Memorial Day, Labor Day, and Columbus Day weekends when vendor counts peak. Approximately 50 vendors fill the property with an impressive mix of antique furniture, vintage tools, Vaseline glassware, estate jewelry, comics, vintage clothing, and folk art, alongside locally-made Vermont maple syrup, organic produce, fresh vegetables, pickles, and artisan crafts. The flea market Vermont experience here distinguishes itself by focusing on genuine antiques and collectibles rather than general merchandise, with pricing described as "very reasonable" though visitors should bring cash as some booths operate cash-only. With free admission and parking, pet-friendly policies, and food concession stands throughout the grounds, this multi-dealer outdoor market has earned 3,994 Facebook likes and glowing reviews praising its friendly vendors, clean Vermont mountain setting, and treasure-hunting atmosphere. Holiday weekends draw the most vendors and largest selection, making these prime times for serious antique shoppers seeking everything from antique tools and Depression glass to upcycling projects and collectible cards. Contact them at Vtflea83@gmail.com or (802) 380-5664 to confirm seasonal opening dates at 236 VT-9, Wilmington, VT 05363.
Located at 79 Main Street in downtown Brattleboro, VT 05301, Boomerang has been Southern Vermont's premier destination for new, used, and vintage clothing since summer 1999—making it a 26-year retail institution. Founded by California transplants Loretta Palazzo and Matt Maranian (a former actress and bestselling author), this award-winning shop was born when the couple fell in love with Brattleboro during a road trip and left Los Angeles behind for Vermont's "sophisticated urban edge." This single-owner boutique—not a multi-dealer shop—specializes in curated vintage fashion, high-end secondhand denim, graphic tees, and artisan-made jewelry from local designers. Boomerang has earned multiple Nextdoor Neighborhood Favorite awards (2020, 2022, 2023) and media recognition from The Boston Globe, Los Angeles Times, New York Post, and Washington Post. Customer reviews praise the "unique vintage and contemporary items" and "friendly, knowledgeable staff," though some note prices can run higher than typical thrift stores—reflecting the shop's curated quality. Open Monday–Saturday 10am–6pm and Sunday 11am–5pm, this compact, well-organized boutique carries brands like Betsey Johnson, Free People, and J. Crew alongside one-of-a-kind vintage pieces. Reach them at (802) 257-6911 or info@boomerangvermont.com for consignment inquiries—they accept trade and consignment but are selective based on 20+ years of customer preferences.
Vermont Marketplace at 580 Canal Street in Brattleboro occupies a historic former handbag factory immediately off I-91 Exit 1 at the Vermont-Massachusetts border. Originally the Brattleboro Outlet Center (a 1980s shopping magnet for national chains like London Fog), the building fell into disrepair until owner Paul Belogour purchased it at auction for approximately $990,000 and invested heavily in renovations including a new roof, repaved parking lot, and refreshed interiors. The marketplace now operates as a "shop local" destination housing approximately 10+ Vermont businesses, open Monday–Saturday 9:30 AM–6 PM and Sunday 9:30 AM–5 PM. The centerpiece is the Vermont Gift Emporium/Exit One Emporium, featuring 60+ local artisans and crafters selling handmade goods, Vermont-made gifts, and rotating artwork—staffed by volunteers and hosting intimate musical shows. Other tenants include Northeast Mountain Footwear (a family-owned boot store in business over 20 years, specializing in work boots and extra-large sizes), The Good Spot wellness lounge offering herbal teas and CBD products, Malisun Boutique with handcrafted Thai jewelry, Mountain Styles Salon & Spa, and Bar 580, an upscale sports bar with a 2,500 square-foot outdoor deck and plans for "580 Provisions" food court featuring four kitchen concepts. For dedicated antique hunting in Brattleboro, visitors should instead check out Twice Upon A Time (10,000 sq ft, 100+ dealers, since 1986) or the Windham Antique Center—but Vermont Marketplace remains an excellent stop for Vermont artisan crafts, local gifts, and farm-to-table dining just over the state line.
Situated at 2026 Harwood Hill Road (Historic Route 7A), Bennington, VT 05201, Covered Bridge Antiques occupies a distinctive building painted "bridge red" and designed to resemble Vermont's famous covered bridges. Opened in December 2020 by owner Raoul Mallalieu—a New Jersey transplant with 35+ years of furniture restoration experience—this 4,000+ square foot multi-dealer antique mall features more than a dozen independent dealers offering everything from estate jewelry and mid-century furniture to military memorabilia and vintage postcards. What sets this Vermont antique shop apart is its on-site furniture restoration workshop, where Mallalieu personally repairs customer heirlooms and shop pieces, emphasizing sustainability and preserving quality craftsmanship "for 10 generations." Prices range from $2 to $2,000 with an average purchase of $15–$30, making it accessible for casual browsers and serious collectors alike. Reviews highlight the "brightly illuminated interior," "open aisles," and "relaxed atmosphere"—a contrast to cluttered antique malls—though some note items are "nice stuff but pricey." The shop specializes in antique furniture, Bennington pottery, vintage cameras, rare books, retro signage, and Victorian-era collectibles. Open Thursday–Monday 10am–5pm (Tuesday–Wednesday by appointment), this antique dealer offers ample parking and a scenic location just north of downtown Bennington. Contact them at (802) 681-4211 or info@antiquesvermont.com.
Flying Horse Estate Sales has been handling Southern Vermont's antique and estate sale needs since 2013, and the backstory is kind of sweet. Owners Ricci and Jim turned their passion into this Manchester VT estate sales business after helping liquidate their own parents' estates. They brought over 20 years of buying and selling experience with them. Their operation runs from 1244 Beech Street in Manchester Center, VT 05255, offering white-glove estate liquidation services throughout Bennington, Dorset, Arlington, Peru, Ludlow, and surrounding communities with comprehensive clean-outs, professional merchandising, and multi-day sales events. Office hours are Monday-Friday 10am-5pm and Saturday 10am-6pm (closed Sundays). Reach them at (802) 362-1537, (802) 375-3492, or flyinghorseantiques@gmail.com. They specialize in high-end antiques: Early American furniture, primitive pieces, designer brands like Drexel Heritage and Ethan Allen, fine art by Eric Sloane and Luigi Lucioni, Bennington Pottery, Waterford crystal, oriental rugs, vintage mid-century furniture, and rare collectibles that draw serious Vermont antique collectors. The numbers back it up too. They've got a 4.6-star Facebook rating with 1,907 followers, plus recognition in the Bennington Banner and Berkshire Eagle for handling everything from small downsizing sales to million-dollar estates with numbered entry systems for their popular Vermont estate auctions. Their sales feature quilts, antique linens, John Deere tractors, woodworking tools, musical instruments, china from Limoges and Wedgwood, fine jewelry, and vintage toys. Whether you need Southern Vermont estate liquidation services or you're hunting for authentic New England antiques, this Manchester estate sale company has built a solid reputation across twelve years of continuous operation.
Burgess Estate Sales has been Southern Vermont's leading estate sale company for over a decade, serving the Manchester, Dorset, Bennington, and Rutland areas from their base at 100 Mad Tom Road in East Dorset. Founded by Bob and Vicki Burgess, the business evolved from Manchester House, their consignment shop on Main Street in Manchester, when a client insisted they needed a full estate sale—that first sale went so well that they never looked back. Following Bob's unexpected passing in January 2022, Vicki Burgess now leads an experienced team that includes a jewelry and antiques specialist, a furniture expert who staged Martha Stewart's charity estate sale, and a professional photographer managing their robust social media presence. The company operates on a commission-only basis with zero upfront costs—signage, advertising, staging, employee wages, and breakdown are all included. Their meticulous process involves surveying every item (they once found a Roman coin in items marked as trash and discovered a Picasso painting at the back of a wine cellar), professional staging, expert pricing, and extensive social media promotion through their Instagram account (@burgessestatesales802, 1,500+ followers). Customer reviews consistently praise their organization, fair pricing, and friendly atmosphere—one Dorset interior designer noted she's attended their sales for years and finds them "always high quality, fair prices and lots of fun." They handle everything from storage unit contents to million-dollar estates, preparing homes to broom-clean condition and specializing in antique furniture, fine art, jewelry, oriental rugs, vintage textiles, and household contents. Contact them at (802) 779-6868 or BurgessEstateSales@gmail.com to schedule a consultation.
The Windham Antique Center at 5 The Square, Bellows Falls, VT 05101 consistently ranks among the finest antique shops in New England, earning a 4.7/5 TripAdvisor rating and Travelers' Choice designation as the #2 attraction in Bellows Falls. Founded in January 2011 by Michael Bruno—a former Tiffany & Co. gemologist from Manhattan—this 7,000-square-foot, two-story multi-dealer antique center was designed to evoke "a turn-of-the-last-century department store" and has operated for 14 years as a centerpiece of downtown revitalization. Bruno's gemological expertise shows in the shop's exceptional jewelry collection, featuring Georgian (1700–1830) and Victorian (1830–1900) era pieces, alongside 18th and 19th century furniture, fossils, minerals, antique clocks, silverware, and fine china. TripAdvisor reviewers call it "part museum, part antique store" and "one of the best Antiques Centers I have ever visited either in North America or other countries," praising the "beautifully curated" displays and "amazing gem section." Pricing offers balance—some reviewers find "very fair and competitive prices" while others note "higher-end" pieces command premium rates. Open daily 10am–5pm year-round, this Vermont antique mall draws interior designers, serious collectors, and other antique dealers who "buy here and sell to other places around the country." The shop occupies a historic building (formerly Sam's Army-Navy store) restored with Vermont tax credits, featuring stunning window displays that have helped transform Bellows Falls' commercial district. Reach them at (802) 732-8081 or windhamantiquecenter@gmail.com.
The Stone House Antique Center at 557 VT Route 103, Chester, VT 05143 stands as Southern Vermont's largest and most diverse antique group shop, spanning an impressive 18,000–20,000 square feet with approximately 90–100 independent dealers under one roof. Operating for more than 20 years in what's often called Vermont's "antique capital," this sprawling multi-dealer antique center has earned a 4.6/5 star rating from approximately 146 reviews and holds the #1 TripAdvisor ranking among Chester attractions, plus a Travelers' Choice award. The center specializes in authentic New England antiques and Americana—"nothing modern"—including antique furniture, Vermont ski lodge décor (vintage sleds, wooden skis, snowshoes), primitives, folk art, depression glass, quilts, militaria, estate jewelry, and rare coins. Reviewers consistently praise the "very reasonable prices," clean and well-lit layout (unusual for antique malls), and helpful staff who will negotiate with vendors on serious purchases—some calling it "one of the most affordable antique stores in Vermont." The shop hosts a popular monthly "Dealer Day" on the first Tuesday of each month featuring special sales and visiting dealers "ready to wheel and deal." Open daily 10am–5pm year-round (closed Easter, Thanksgiving, Christmas Eve, and Christmas Day), the center offers ample free parking, wheelchair accessibility, and air conditioning. Located just outside Chester's village center and accessible from I-91 Exit 6, this Vermont antique mall makes an ideal stop when exploring the region's covered bridges and historic stone village. Contact them at (802) 875-4477 or shac@vermontel.net.
Country Treasures Quilt Shop at 12 The Common in Chester, Vermont has been a quilting mecca since 1990—35 years of continuous operation—making it one of New England's premiere quilt destinations. Founded by Sue Ashe, who owned and operated it for over 31 years, the shop was purchased in September 2021 by Angela Farrar, a Chester native whose passion for sewing tote bags evolved into an obsession with collecting beautiful fabrics. The shop is housed in a historic building with six rooms spread across an old country house, featuring an entire room dedicated to flannel, sections organized by color, and a generous sale room in the back with discounted fabrics. The inventory is staggering: over 6,000 bolts of quilting fabric and 10,000+ fat quarters, including extensive batiks, homespuns, reproduction fabrics, novelty prints, and seasonal patterns. Quilters travel hours specifically to visit—one reviewer called it "perhaps the finest and most complete quilt store I have ever had the pleasure of shopping"—earning it a 4.7-star rating from 66 reviews. The shop participates in the Vermont Shop Hop and Row by Row Experience, offers quilting classes six days a week for all skill levels, and Sue Ashe continues offering sought-after long-arm quilting services from Sue's Quilt Studio in the back. Hours are Wednesday–Saturday 9 AM–4 PM and Sunday 12–4 PM (closed Mondays, Tuesdays, and the first two weeks of April for mud season). They even sell Vermont maple syrup made in their own sugar house—reach them at (802) 875-4377.
The Chester-Andover Family Center has been serving the Chester and Andover communities since 1996—nearly 29 years as a 501(c)(3) nonprofit providing essential services through three programs: a well-stocked thrift shop, food shelf, and emergency financial assistance. Located at 908 VT-103 South in Chester, the thrift shop is the primary revenue source funding all community programs, earning a three-star Charity Navigator rating for accountability and transparency. In April 2024, the thrift shop expanded and hired a new manager, Mike Antowitz, extending hours to serve more customers—it's now open Thursday 9 AM–7 PM, Friday 10 AM–4 PM, and Saturday 9 AM–4 PM. The inventory includes clothing for all ages (sorted, cleaned, sized, and steamed), footwear, jewelry, household goods, small appliances (all tested for functionality), books, DVDs, linens, toys, and occasional furniture and antiques—many items arrive new with tags still on. Reviewers praise the affordable prices, well-organized layout, and friendly volunteer staff who greet customers with "a smile and a great deal" while keeping the coffee pot always plugged in. The center hosts half-price sales on clothing and accessories throughout the year, and their 11th annual Warm Hands Warm Hearts drive distributes hundreds of free coats, boots, and blankets to anyone in need. Their 6th Annual Empty Bowl Dinner in November 2024 raised $12,828 for community programs. Beyond bargain hunting, every purchase directly supports neighbors facing heating bills, rent emergencies, or food insecurity—donate items during open hours or shop guilt-free knowing your dollars stay local.
